2-溴喹啉 | 2005-43-8

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-溴喹啉
• 中文别名: 2-溴喹
• 英文名称: 2-bromoquinoline
• 英文别名: bromo-quinoline
• CAS: 2005-43-8
• 化学式: C₉H₆BrN
• 分子量: 208.057
• InChiKey: QKJAZPHKNWSXDF-UHFFFAOYSA-N

物化性质

• 熔点：
  44-48 °C
• 沸点：
  115°C/0.3mmHg(lit.)
• 密度：
  1.564±0.06 g/cm3(Predicted)
• 闪点：
  >110℃
• 溶解度：
  溶于甲醇
• 最大波长(λmax)：
  319nm(EtOH)(lit.)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，没有已知的危险反应，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933499090
• 危险品运输编号：
  NONH for all modes of transport
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H315,H318,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338
• 储存条件：
  请将贮藏器保持密封，并存放在阴凉、干燥处。同时，确保工作环境具有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromoquinoline
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromoquinoline
CAS number: 2005-43-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H6BrN
Molecular weight: 208.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

溴喹啉

溴喹啉有七种位置异构体，其主要物性列表如下：

名称	熔点(℃)	沸点(℃)	溶解性
2-溴喹啉	48～49	-	易溶于乙醚、氯仿、苯
3-溴喹啉	12～15	274～276、95(66.66Pa)	-
4-溴喹啉	29～30	270(分解)	易溶于稀酸
5-溴喹啉	52(针状晶体)	280	-
6-溴喹啉	24	278	-
7-溴喹啉	52(针状晶体)	290	-
8-溴喹啉	80	165～166 (2399.79Pa)	-

用途和制备方法

• 3-溴喹啉：与混酸作用生成3-溴-5-硝基喹啉，进一步被氧化为5-溴-2,3-吡啶二甲酸。
• 6-溴喹啉：与硝酸加热生成6-溴-8-硝基喹啉，再与高锰酸钾作用被氧化为2,3-吡啶二甲酸。

合成方法如下：

1. 由2-羟基喹啉与五溴化磷作用制得2-溴喹啉。
2. 由喹啉过溴化物于180℃加热制得3-溴喹啉。
3. 由4-羟基喹啉与五溴化磷加热，或由4-氨基喹啉经重氮化反应制得4-溴喹啉。
4. 5-溴喹啉由间溴苯胺、甘油、间溴硝基苯及浓硫酸加热，或由5-氨基喹啉经重氮化反应制取。
5. 6-溴喹啉由对溴苯胺与甘油、浓硫酸、对溴硝基苯加热制得。
6. 7-溴喹啉由7-氨基喹啉经重氮化反应制得。
7. 8-溴喹啉由邻溴苯胺、甘油、浓硫酸及邻溴硝基苯加热制得。

用途：作为有机合成试剂。

反应信息

• 作为反应物：
  描述：

  2-溴喹啉 在 偶氮二异丁腈 、 三正丁基氢锡 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 喜树碱
  参考文献：
  名称：

  喜树碱生物碱的不对称合成：（S）-喜树碱的九步合成

  摘要：

  由2-氯-6-羟基吡啶经六个步骤对映选择性地制备DE环喜树碱中间体II，并将其用于（S）-喜树碱的九步合成。

  DOI：

  10.1016/s0040-4039(00)73492-7
• 作为产物：
  描述：

  1-甲基-2-喹啉酮 在 1,3-二溴-1,3,5-三嗪-2,4,6-三酮 、 三苯基膦 作用下， 以 neat (no solvent) 为溶剂， 反应 16.0h， 以78%的产率得到2-溴喹啉
  参考文献：
  名称：

  Development of a Facile and Inexpensive Route for the Preparation of α-Halobenzopyridines from α-Unsubstituted Benzopyridines

  摘要：

  A facile and inexpensive route for the preparation of alpha-halobenzopyridines from alpha-unsubstituted benzopyridines via N-methylbenzopyridin-alpha-ones was developed. alpha-Unsubstituted benzopyridines were converted easily into the corresponding N-methylbenzopyridin-alpha-ones, which were halogenated using PPh3-TCICA or PPh3-DBICA without using solvent to give a-halobenzopyridines.

  DOI：

  10.3987/com-15-13234
• 作为试剂：
  描述：

  8-bromo-4-[(3-chlorophenyl)amino]-6-[(pyridin-3-ylmethyl)amino]quinoline-3-carbonitrile 、 N,N-二甲基甲酰胺 在 Zinccyanide 、 四(三苯基膦)钯 2-溴喹啉 、 乙酸乙酯 、 Brine 、 magnesium sulfate 、 crude product 作用下， 反应 0.25h， 以to give a fluffy yellow solid (6.9 mg, 7.8% yield)的产率得到4-(3-Chlorophenylamino)-6-(pyridin-3-ylmethylamino)quinoline-3,8-dicarbonitrile
  参考文献：
  名称：

  3-Cyanoquinoline inhibitors of Tpl2 kinase and methods of making and using the same

  摘要：

  本发明提供公式（I）的化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、m和n的定义如本文所述。本发明还提供制备公式（I）化合物的方法，以及治疗炎症性疾病（如类风湿性关节炎）的方法，包括向哺乳动物投与公式（I）化合物的治疗有效量。

  公开号：

  US20060264460A1

文献信息

• 一种硅立体中心手性化合物及其合成方法
  申请人：杭州师范大学

  公开号：CN108558927B

  公开（公告）日：2020-06-19

  本发明本发明涉及化学合成技术领域，为解决目前硅立体中心手性硅烷合成方法中存在诸如底物适用性差、化学选择性和立体选择性不高的问题，本发明提出了一种硅立体中心手性化合物及其合成方法，以烷基二芳基氮杂芳环硅烷化合物为原料，与烯烃反应合成高对映选择性的硅立体中心手性硅烷，条件温和、反应物廉价、制备方法简便。
• Desymmetrization‐Oriented Enantioselective Synthesis of Silicon‐Stereogenic Silanes by Palladium‐Catalyzed C−H Olefinations
  作者：Yan Lin、Wei‐Yang Ma、Zheng Xu、Zhan‐Jiang Zheng、Jian Cao、Ke‐Fang Yang、Yu‐Ming Cui、Li‐Wen Xu

  DOI：10.1002/asia.201900408

  日期：2019.6.14

  A palladium‐catalyzed chelation‐assisted enantioselective C−H olefination of symmetrically diaryl‐substituted tetraorganosilicon derivatives was developed, enabling the generation of nitrogen‐containing silicon‐stereogenic tetraorganosilicon compounds with modest to good yields and good to excellent enantioselectivities (up to 95.5:4.5 e.r.). The Thorpe–Ingold effect exerted by the substituents on

  已开发出钯催化的对称二芳基取代的四有机硅衍生物的螯合辅助对映选择性C H烯化反应，能够生成产率适中至良好且优良至优异对映选择性的含氮硅立体异构四有机硅化合物（高达95.5：4.5） er）。观察到，取代基在硅上产生的索普-英戈尔德效应对烯化产物的形成有深远的影响，该产物进一步转化为其他相关的手性有机硅烷，而不会损失对映体纯度，因此证明了已开发的对映选择性烯化的合成效用。
• Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
  作者：Yajun Liu、Jihye Kim、Heesun Seo、Sunghyouk Park、Junghyun Chae

  DOI：10.1002/adsc.201400941

  日期：2015.7.6

  single‐step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2‐ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high

  利用铜（II）催化剂和1,2-乙二硫醇开发了一种高效的过渡金属催化的从芳基卤化物单步合成芳基硫醇的方法。关键特征是使用现成的试剂，简单的操作以及相对温和的反应条件。该新协议显示了广泛的底物范围，具有出色的官能团相容性。由芳基卤化物直接以高收率制备各种芳基硫醇。此外，芳基硫醇原位用于合成更高级的分子，例如二芳基硫醚和苯并噻吩。
• Water-Sculpting of a Heterogeneous Nanoparticle Precatalyst for Mizoroki–Heck Couplings under Aqueous Micellar Catalysis Conditions
  作者：Haobo Pang、Yuting Hu、Julie Yu、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1021/jacs.0c11484

  日期：2021.3.10

  Powdery, spherical nanoparticles (NPs) containing ppm levels of palladium ligated by t-Bu3P, derived from FeCl3, upon simple exposure to water undergo a remarkable alteration in their morphology leading to nanorods that catalyze Mizoroki–Heck (MH) couplings. Such NP alteration is general, shown to occur with three unrelated phosphine ligand-containing NPs. Each catalyst has been studied using X-ray

  粉末状球形纳米粒子 (NPS) 含有 ppm 级的钯，由来自 FeCl 3的t- Bu 3 P连接，在简单暴露于水中后，其形态发生显着变化，导致纳米棒催化 Mizoroki-Heck (MH) 偶联。这种 NP 改变是普遍的，显示发生在三个不相关的含膦配体的 NP 中。已使用 X 射线光电子能谱 (XPS)、能量色散 X 射线能谱 (EDX)、透射电子显微镜 (TEM) 和低温透射电子显微镜 (cryo-TEM) 分析研究了每种催化剂。专门依赖于含有t- Bu 3 的NPS 的联轴器P-连接的 Pd 在室温至 45 °C 之间的水性胶束催化条件下发生，并显示出广泛的底物范围。与这项新技术相关的其他关键特性包括产品中残留的 Pd 低、水性反应介质的循环利用以及相关的低 E 因子。galipinine 是汉考克生物碱家族的一员，其前体的合成暗示了潜在的工业应用。
• Nickel‐Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry
  作者：Dong Liu、Hong‐Xing Ma、Ping Fang、Tian‐Sheng Mei

  DOI：10.1002/anie.201900956

  日期：2019.4

  Transition‐metal‐catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition‐metal‐catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel‐catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence

  过渡金属催化的偶联反应是合成芳基硫化合物的有用工具。但是，常规的过渡金属催化的芳基溴化物和氯化物的硫醇化反应通常需要在升高的反应温度下使用强碱。在此，我们报道了在室温下使用不分隔的电化学电池，在不存在外部碱的情况下，镍催化的芳基溴化物和氯化物的电化学催化硫醇化反应的第一个实例。